Synthesis of steroids



United States Patent 3,344,149 SYNTHESIS OF STEROIDS Patrick A. Diassi,Westfield, N.J., assignor, by mesne assignments, to E. R. Squibb & Sons,Inc., New York, N.Y., a corporation of Delaware N0 Drawing. Originalapplication Feb. 3, 1964, Ser. No. 342,263, now Patent No. 3,278,556,dated Oct. 11, 1966. Divided and this application Mar. 9, 1966, Ser. No.

1 Claim. (Cl. 260-3433.)

This application is a divisional application of US. application, SerialNo. 342,263, filed February 3, 1964, now having matured to US.3,278,556.

This invention relates to the provision of novel physiologically activecompounds and more particularly to a compound of the formula EXAMPLE11B-hydroxy-A -dehydrotestololactone To a solution of 170 mg. of11-keto-A -dehydr0testololactone in 25 ml. of tetrahydrofuran, freshlydistilled from 3,344,149 Patented Sept. 26, 1967 lithium aluminumhydride, 340 mg. of lithium tri-t-butoxy aluminum hydride are added andthe mixture stirred un der nitrogen at room temperature for twenty-fourhours. The reaction mixture is then carefully diluted with ml. of 10%acetic acid and extracted with chloroform. The chloroform extracts areWashed with water, dried over sodium sulfate, and evaporated to dryness.Crystallization of the residue from methanol gives 136 mg. ofllfi-hydroxy-A -dehydrotestololactone having a melting point 238-240",-37 the nl MS...

Analysis.-Calcd for C H O (316.38): C, 72.12; H, 7.65. Found: C, 72.03;H, 7.79.

The invention may be variously otherwise embodied within the scope ofthe appended claim.

What is claimed is:

A process for preparing 11,B-hydroxy-A -dehydrotestololactone whichcomprises reacting ll-keto-A -dehydrotestololactone with lithiumtri-t-butoxy aluminum hydride.

References Cited UNITED STATES PATENTS 2,855,404 10/1958 Richards260-343.2 2,946,807 7/1960 Fried et a1. 260343.2 3,258,470 6/1966 Cross260--343.2

OTHER REFERENCES Herr et al., Jour. Amer. Chem. Soc., volume (1953),pages 5927 to 5930.

Herr et al., Jour. Amer. Chem. 800., volume 78 (1956), pages 500 to 501.

WALTER A. MODANCE, Primary Examiner. J. PATTEN, Assistant Examiner.

